![4-[(2-Fluoro-4-methylphenyl)amino]-6-[4-(2-hydroxyethyl)-1-piperazinyl]-7-methoxy-3-cinnolinecarboxamide structure](https://static.chemtradehub.com/structs/104/1041852-85-0-fb1c.webp "4-[(2-Fluoro-4-methylphenyl)amino]-6-[4-(2-hydroxyethyl)-1-piperazinyl]-7-methoxy-3-cinnolinecarboxamide structure")
4-[(2-Fluoro-4-methylphenyl)amino]-6-[4-(2-hydroxyethyl)-1-piperazinyl]-7-methoxy-3-cinnolinecarboxamide
CAS Number:
1041852-85-0
Molecular Formula:
C23H27FN6O3
Radical heteroarylation of unactivated remote C(sp3)–H bonds via intramolecular heteroaryl migration
Literature Information
Publication Date
2021-09-20
DOI
10.1039/D1QO01209F
Impact Factor
5.281
Authors
Zhu Cao, Huihui Zhang, Xinxin Wu, Yahong Li
View Original
Abstract
The radical-mediated heteroarylation of unactivated remote C(sp3)–H bonds via intramolecular heteroaryl migration is achieved, leading to a variety of heteroaryl-substituted aliphatic ketones. A library of O-/S-/N-containing heteroaryls such as benzofuryl, benzothiazolyl, benzothienyl, benzoxazolyl, oxazolyl, and thiazolyl are amenable to the migration approach. The heteroaryl migration is triggered by an azido radical-mediated hydrogen atom abstraction from unactivated aliphatic C(sp3)–H bonds. The transformation features mild C–C bond cleavage, good selectivity for tertiary C(sp3)–H bonds, and broad functional group compatibility.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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